Ok. Here is a stumper. We are running google apps sync along with outlook 2010. We had a situation where a user created an email that had a little under 2.5MB in attachments. When they attempted to send it out all it did was just sit in their outbox. The sent progress indicator did indicate that the email had sent. However, when checking with Google and the server, it had no record of the document ever being created, much less attempted to be sent out. Needless-to-say, I had a rather pissed off director at the loss of a message that there was no record of ever being created.

A little more information: as part of the troubleshooting I attempted to resync outlook and google apps as well as save the email in outlook as well. According to outlook, the email saved so I closed out the program and brought it back up. It still never sent the stuck email so I deleted it (after all, I had saved a copy of it) only to find that the save appears to have been an image of outlook, but not the email.

In short, it appears that the original email that was stuck in the outbox never existed. Has anybody every come across something like that? What can be done to prevent this from happening in the future?

6 Replies

I have occasionally seen emails stick in the Outbox. This isn't unique to a user on Outlook 2010 or someone using GASMO (we had it happen on our old POP mail server as well as after migrating to Apps), it seems to be an Outlook problem. The email doesn't appear to have anything wrong with it, but it simply won't send. Emails sent after it sometimes also get stuck in the Outbox as well, until you clear out the problem email. You basically have to delete the email from the Outbox, then recreate it. No idea what causes it, but I have seen this behavior, or something that's very similar.

One suggestion, since you're using GASMO. There's a set of trace (log) files in c:\users\username\appdata\local\google\google apps sync\tracing folder. You can grab a file from the time this occurred, and submit it to Google's automated log analyzer at https://www.google.com/apps/support/tools/migration_sync/outlook-sync and see what they say. I've had mixed luck with the log files, but it's worth a shot.

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Allen and Chris; the size of the attachments totaled a little over 2mbs so I don't believe file attachment size is an issue here and no we do not run Kaspersky of any kind. We do run Comodo, so there could be some similarities, but the hang up appears to only affect this one machine. I am not sure, but I am guessing this message may have been open for a long period of time before it was attempted to be sent. So, could that possibly be at play?

Paul, I actually have sent a log file to google. You are right on the money, sometimes their results are hit or miss. However, it gave them something to chew on so that isn't bad either. At the end of the day, just a work around to avoid this in the future I think would be worth it's weight in gold. As the old adage goes, a ounce of prevention is worth a pound of cure.

GASMO runs as an Outlook Add-on. If you have other add-ons on this machine, they may be conflicting. If this is the case, you may need to uninstall and reinstall GASMO and the other add-ons. It is not uncommon for the order of installation to matter.

Has the user added any tools since GASMO was installed on this machine?